About the job

We’re helping fuel the growth of American lower middle market businesses. High Street Capital isn’t your typical private equity firm. For nearly three decades, we’ve partnered with entrepreneurs, operators, and executives to turn good businesses into great ones. With $247.5 million of capital raised for our Fund VI, we’re doubling down on what we do best: building companies, empowering management teams, and creating long-term value. Our culture thrives on curiosity, collaboration, and a shared passion for helping hard-working people to build their businesses. 

At High Street Capital, we roll up our sleeves and work side by side with management teams, supported by seasoned Operating Partners who bring real operating expertise to the table. Integrity, excellence, and respect have guided us for 28 years and remain the foundation of our success. We build authentic partnerships through equity alignment, open communication, and a shared vision that keeps everyone moving in the same direction. For Associates, that means meaningful responsibility from day one—contributing directly to investments, portfolio growth, and the lasting impact we create together. High Street Capital is based in Chicago, IL. 

What You’ll Do. Associates are integral members of the investment team. From day one, you’ll take on meaningful responsibility and contribute across the full investment lifecycle—from sourcing and evaluating opportunities to supporting portfolio company growth. The role builds on your prior experience while affording you exposure to a wide range of opportunities that will further develop your skills and perspective in private equity. 

• Screening New Investments: Identify and evaluate new opportunities, manage information flow, and coordinate key legal documentation (NDAs, CIMs, etc.). 
• Financial Analysis: Build financial models, perform valuations, and provide data-driven insights that shape investment decisions. 
• Industry & Market Research: Go deep on sectors and trends to uncover where real opportunities lie. 
• Due Diligence: Lead diligence efforts, collaborate with third-party providers, and ensure investment theses and analyses are rock-solid. 
• Deal Execution: Support negotiations and review documentation for acquisitions, add-ons, financings, and amendments. 
• Investment Materials: Craft clear, compelling memos that distill complexity into actionable insights for the Investment Committee. 
• Portfolio Monitoring: Track performance through monthly financials, oversee quarterly valuations, and prepare reporting packages. 
• Business Development: Contribute to sourcing, thematic research, and investor relations—Associates here get broad exposure, not narrow lanes.

What We’re Looking For. We’re seeking a resourceful, driven professional who thrives in entrepreneurial settings and is eager to contribute meaningfully to a close-knit investment team. 

• Bachelor’s degree with outstanding academic performance
• 2+ years in investment banking, consulting, transaction advisory, or private equity 
• Proven strength in financial modeling, valuation, and company analysis 
• Sharp analytical and research skills paired with sound judgment 
• Mastery of Excel, PowerPoint, and Word 
• Strong communicator with the ability to distill insights and build trust with stakeholders 
• Self-starter with a bias for action and impeccable attention to detail 
• Comfortable working independently and in small, highly collaborative deal teams 
• Professional maturity and the ambition to grow with the firm 

Please send resumes to recruiting@highstreetcapital.com.